Methanol → methyl 2-(1-methyl-1H-indol-3-yl)pentanoate

HRID 590998Notes

Reaction equation

HRID 590998 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]([CH2:15][CH2:16][CH3:17])[C:12]([OH:14])=[O:13])=[CH:3]1.S(=O)(=O)(O)O.[CH3:23]O>>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]([CH2:15][CH2:16][CH3:17])[C:12]([O:14][CH3:23])=[O:13])=[CH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 708180292-(1-methyl-1H-indol-3-yl)pentanoic acid

Product 1

HCID 70817995methyl 2-(1-methyl-1H-indol-3-yl)pentanoateYield 70%

Procedure

A mixture of 2-(1-methyl-1H-indol-3-yl)pentanoic acid (12a) (1.22 g, 5.28 mmol) and concentrated sulfuric acid (1 mL) in methanol (40 mL) was refluxed for 3 hours. After concentration, the mixture was quenched with a saturated aqueous solution of sodium carbonate and the aqueous layer was extracted with dichloromethane (2×20 mL). The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 93/7) to afford the desired ester (12b) as a white solid (910 mg, 3.71 mmol, 70%).

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationAfter concentration
  3. customthe mixture was quenched with a saturated aqueous solution of sodium carbonate
  4. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 93/7)

Sources & evidence

ORD record
ord-e8ccd2e7c7ed478fa43c499b09224447
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

Loading…